Jun 25, 2026

SUMMARY

True wealth planning goes beyond spreadsheets and tax returns. That's the premise behind Heidi Olson's work at Pathfinder Legacy, and it's what drew Tom to have her on the show. In this conversation, Heidi shares how she helps families, farmers, and business owners move past the discomfort of estate and...

Jun 18, 2026

Summary

This episode is part two of a series covering Tom’s due diligence trip to Raleigh, North Carolina, where he evaluated a multifamily real estate syndication opportunity. This time, Tom is joined by his son Aidan, a college student who came along for the trip and got a firsthand look at how private real estate...

Jun 11, 2026

Summary

Every advisor, every CPA, every financial professional has heard it: “I’m paying way too much in taxes.” And while that pain is real, I’ve noticed something important when I dig a little deeper with clients. The taxes themselves are often the most visible and most painful part of a much larger problem....

Jun 4, 2026

Summary

There's a certain kind of financial education that never shows up in a classroom or on a balance sheet, and that's what Tom set out to give his son on a recent trip to the Raleigh, North Carolina area. Alongside touring a multifamily syndication investment, Tom used the experience to open the door on how...